JP7446711B2 - 皮膚外用組成物 - Google Patents
皮膚外用組成物 Download PDFInfo
- Publication number
- JP7446711B2 JP7446711B2 JP2018238235A JP2018238235A JP7446711B2 JP 7446711 B2 JP7446711 B2 JP 7446711B2 JP 2018238235 A JP2018238235 A JP 2018238235A JP 2018238235 A JP2018238235 A JP 2018238235A JP 7446711 B2 JP7446711 B2 JP 7446711B2
- Authority
- JP
- Japan
- Prior art keywords
- retinol
- skin
- component
- allantoin
- antipruritic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000000203 mixture Substances 0.000 title claims description 74
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 96
- POJWUDADGALRAB-UHFFFAOYSA-N allantoin Chemical compound NC(=O)NC1NC(=O)NC1=O POJWUDADGALRAB-UHFFFAOYSA-N 0.000 claims description 48
- 235000020944 retinol Nutrition 0.000 claims description 48
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 claims description 45
- 230000001139 anti-pruritic effect Effects 0.000 claims description 43
- 239000011607 retinol Substances 0.000 claims description 41
- 229960003471 retinol Drugs 0.000 claims description 41
- -1 chlorohydroxyaluminum Chemical compound 0.000 claims description 24
- 229960000458 allantoin Drugs 0.000 claims description 23
- POJWUDADGALRAB-PVQJCKRUSA-N Allantoin Natural products NC(=O)N[C@@H]1NC(=O)NC1=O POJWUDADGALRAB-PVQJCKRUSA-N 0.000 claims description 22
- 229960000520 diphenhydramine Drugs 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000003908 antipruritic agent Substances 0.000 claims description 12
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 12
- 239000000194 fatty acid Substances 0.000 claims description 12
- 229930195729 fatty acid Natural products 0.000 claims description 12
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- 239000000126 substance Substances 0.000 claims description 8
- MPDGHEJMBKOTSU-YKLVYJNSSA-N 18beta-glycyrrhetic acid Chemical compound C([C@H]1C2=CC(=O)[C@H]34)[C@@](C)(C(O)=O)CC[C@]1(C)CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@H](O)C1(C)C MPDGHEJMBKOTSU-YKLVYJNSSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 claims description 4
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- 239000011732 tocopherol Substances 0.000 claims description 4
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- JDLSRXWHEBFHNC-UHFFFAOYSA-N Ufenamate Chemical compound CCCCOC(=O)C1=CC=CC=C1NC1=CC=CC(C(F)(F)F)=C1 JDLSRXWHEBFHNC-UHFFFAOYSA-N 0.000 claims 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical compound C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims 2
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- 210000003491 skin Anatomy 0.000 description 62
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- 229940079593 drug Drugs 0.000 description 7
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 description 4
- 239000000739 antihistaminic agent Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000004624 Dermatitis Diseases 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 239000004166 Lanolin Substances 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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- FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 208000010668 atopic eczema Diseases 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 235000019388 lanolin Nutrition 0.000 description 3
- 229940039717 lanolin Drugs 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 235000019155 vitamin A Nutrition 0.000 description 3
- 239000011719 vitamin A Substances 0.000 description 3
- 229940045997 vitamin a Drugs 0.000 description 3
- 239000001993 wax Substances 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 2
- ASKIVFGGGGIGKH-UHFFFAOYSA-N 2,3-dihydroxypropyl 16-methylheptadecanoate Chemical compound CC(C)CCCCCCCCCCCCCCC(=O)OCC(O)CO ASKIVFGGGGIGKH-UHFFFAOYSA-N 0.000 description 2
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 2
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- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
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- 241000723346 Cinnamomum camphora Species 0.000 description 2
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- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- HVUCRESARJLKJG-UHFFFAOYSA-K trisodium 1-hexadecoxyhexadecane phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O.CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC HVUCRESARJLKJG-UHFFFAOYSA-K 0.000 description 1
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- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229960001296 zinc oxide Drugs 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
項1. (A)ジフェンヒドラミン及び/又はその塩、(B)レチノール及び/又はその誘導体、並びに(C)アラントイン及び/又はその誘導体を含有する皮膚外用組成物。
項2. 鎮痒用途で使用される、項1に記載の皮膚外用組成物。
項3. 前記(C)成分の含有量が0.001~10重量%である、項1又は2に記載の皮膚外用組成物。
項4. 前記(A)成分1重量部当たりの前記(C)成分の含有量が0.001~10重量部である、項1~3のいずれかに記載の皮膚外用組成物。
項5. (A)ジフェンヒドラミン及び/又はその塩並びに(B)レチノール及び/又はその誘導体を含む皮膚外用組成物において、鎮痒効果を向上させる方法であって、
皮膚外用組成物に、前記(A)成分及び前記(B)成分とともに(C)アラントイン及び/又はその誘導体を配合する、鎮痒効果向上方法。
本発明の皮膚外用組成物は、(A)ジフェンヒドラミン及び/又はその塩(以下、「(A)成分」とも記載する。)、(B)レチノール及び/又はその誘導体(以下、「(B)成分」とも記載する。)、及び(C)アラントイン及び/又はその誘導体(以下「(C)成分」とも記載する。)を含有することを特徴とする。以下、本発明の皮膚外用組成物について詳述する。
本発明の皮膚外用組成物は、(A)成分としてジフェンヒドラミン及び/又はその塩(以下において、ジフェンヒドラミン類とも記載する)を含有する。ジフェンヒドラミンは、抗ヒスタミン作用があることが知られている公知の薬剤である。(A)成分は単独でも鎮痒作用を奏するが、本発明の皮膚外用組成物は、更に向上した鎮痒性を発揮することが可能である。
本発明の皮膚外用組成物は、(B)成分としてレチノール及び/又はその誘導体を含有する。レチノールは、ビタミンAの1種であり、ビタミンAアルコールとも称されることがある成分である。
本発明の皮膚外用組成物は、(C)成分としてアラントイン及び/又はその誘導体(以下において、アラントイン類とも記載する)を含んでいてもよい。アラントイン類は組織修復作用で知られているが、本発明では、レチノール類の存在下でジフェンヒドラミン類と組み合わせられることで、ジフェンヒドラミン類による鎮痒作用を飛躍的に上回る、高い鎮痒効果を発現することができる。
本発明の皮膚外用組成物は、前述する成分の他に、必要に応じて、他の薬理成分を含んでもよい。このような薬理成分としては、例えば、抗ヒスタミン剤(マレイン酸クロルフェニラミン等)、局所麻酔剤(リドカイン、ジブカイン、プロカイン、テトラカイン、ブピバカイン、メピバカイン、クロロプロカイン、プロパラカイン、メプリルカイン又はこれらの塩、安息香酸アルキルエステル(例えばアミノ安息香酸エチル、塩酸パラブチルアミノ安息香酸ジエチルアミノエチル)、オルソカイン、オキセサゼイン、オキシポリエントキシデカン、ロートエキス、ペルカミンパーゼ、テシットデシチン等)、抗炎症剤(ウフェナマート、グリチルレチン酸、グリチルレチン酸塩、サリチル酸、サリチル酸グリコール、サリチル酸メチル、インドメタシン、フェルビナク、ジクロフェナクナトリウム、ロキソプロフェンナトリウム等)、殺菌剤(酸化亜鉛、塩化ベンザルコニウム、塩化デカリニウム、塩化ベンゼトニウム、塩化セチルピリジニウム、イソプロピルメチルフェノール、塩酸クロルヘキシジン、グルコン酸クロルヘキシジン、アンモニア水、スルファジアジン、乳酸、フェノール等)、鎮痒剤(クロタミトン、チアントール等)、皮膚保護剤(コロジオン、ヒマシ油等)、血行促進成分(ノニル酸ワニリルアミド、ニコチン酸ベンジルエステル、カプサイシン、トウガラシエキス等)、清涼化剤(メントール、カンフル等)、ビタミン類(ビタミンB,C,D,E等)、ムコ多糖類(コンドロイチン硫酸ナトリウム、ヒアルロン酸等)等が挙げられる。
本発明の皮膚外用組成物の性状としては特に限定されず、水性液状組成物、水性ゲル状組成物、油性ゲル状組成物、油性組成物、乳化組成物等が挙げられる。これらの性状の中でも、好ましくは乳化組成物が挙げられる。
本発明の皮膚外用組成物は、鎮痒用途に使用することができ、痒みを感じる皮膚の部位又は掻痒を防止すべき皮膚の部位に塗布することにより使用される。本発明の皮膚外用組成物が適用される皮膚の部位における皮膚症状としては、痒みが惹起される症状であれば特に限定されないが、毛穴炎症、赤み、湿疹、かぶれに対して好ましく適用される。
上述するように、アラントイン類は、ジフェンヒドラミン類及びレチノール類を含む皮膚外用組成物の鎮痒効果を飛躍的に向上させる。従って、本発明は、更に、ジフェンヒドラミン類及びレチノール類を含む皮膚外用組成物の鎮痒効果を向上させる方法を提供する。具体的には、本発明の鎮痒効果向上方法は、皮膚外用組成物に、(A)ジフェンヒドラミン及び/又はその塩、並びに(B)レチノール及び/又はその誘導体とともに(C)アラントイン及び/又はその誘導体を配合することを特徴とする。本発明の鎮痒効果向上方法において、使用される成分の種類や配合量、皮膚外用組成物の性状・製剤形態、使用方法等については、前記「1.皮膚外用組成物」の欄に記載の通りである。
表1に示す組成の皮膚外用組成物を調製した。具体的には、表1に示す各成分を秤量及び混合し、65~75℃で均一溶解状態とした。その後、放置して室温まで冷却し、皮膚外用組成物を得た。
使用動物
種 マウス
系統 Slc:ICR
週齢 5週齢
入手元 日本エスエルシー(株)
掻痒惹起物質の投与
掻痒惹起物質 Compound 48/80
入手元 Sigma-Aldrich Co.
投与経路 皮内投与
投与用量 50μg/site
投与方法 ガラス製注射筒((株)トップ)及び30Gニードル((株)デントロニクス)を用いて、剃毛し皮膚外用組成物を塗布した直後の背部に投与した。
投与回数 1回
投与経路 塗布
投与用量 100mg/マウス
投与方法 掻痒惹起物質投与直前に、ゴム手袋をした指で、剃毛した背部全体に塗り広げた。
投与回数 1回
Windows Media Player(バージョン:12.0.7601.23517)によりビデオ映像中のマウスの行動を観察し、マウス後肢によるマウスの背部への掻き動作を、掻痒惹起物質投与直後~掻痒惹起物質投与後15分経過時の間で、何回行ったかをカウントした。掻き動作の回数は、マウスが引っ掻くために後肢を上げ、引っ掻き行動を行って再び後肢を下す一連の動作を完了した時点で1回とした。カウントには連式数取器(DS-404:高野計器(株))を使用し、映像が途中で切れていないことを映像中のタイマー表示で確認した。
カウントした掻き動作回数と、参考例1(コントロール)における掻き動作回数と、比較例1における掻き動作回数とから、以下に基づいて鎮痒指数を導出した。鎮痒指数が高いほど、鎮痒効果が高いことを示す。結果を表1に示す。
Claims (4)
- (A)ジフェンヒドラミン及び/又はその塩、(B)レチノール、レチノールと炭素数1~30の脂肪酸とのエステル、及び/又はレチノールの酸化物、並びに(C)アラントイン、アラントインクロルヒドロキシアルミニウム、及び/又はアラントインヒドロキシアルミニウムを含有し、鎮痒用途で使用される、皮膚外用組成物(但し、[i]グリチルレチン酸、トコフェロール酢酸エステル、及びイソプロピルメチルフェノールを含むもの、[ii]ヘパリン類似物質を含むもの、並びに、[iii]ウフェナマート及びトコフェロールエステルを含むものを除く)。
- 前記(C)成分の含有量が0.001~10重量%である、請求項1に記載の皮膚外用組成物。
- 前記(A)成分1重量部当たりの前記(C)成分の含有量が0.001~10重量部である、請求項1又は2に記載の皮膚外用組成物。
- (A)ジフェンヒドラミン及び/又はその塩並びに(B)レチノール、レチノールと炭素数1~30の脂肪酸とのエステル、及び/又はレチノールの酸化物を含み、鎮痒用途で使用される皮膚外用組成物(但し、[i]グリチルレチン酸、トコフェロール酢酸エステル、及びイソプロピルメチルフェノールを含むもの[ii]ヘパリン類似物質を含むもの、並びに、[iii]ウフェナマート及びトコフェロールエステルを含むものを除く)において、鎮痒効果を向上させる方法であって、
皮膚外用組成物に、前記(A)成分及び前記(B)成分とともに(C)アラントイン、アラントインクロルヒドロキシアルミニウム、及び/又はアラントインヒドロキシアルミニウムを配合する、鎮痒効果向上方法。
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